4-(Methylthio)phenylboronic acid → 1-Methylsulfanyl-4-[2-(4-methylsulfonylphenyl)-1-cyclopentenyl]benzene

HRID 37531

반응식

HRID 37531 반응식
Br[C:2]1[CH2:6][CH2:5][CH2:4][C:3]=1[C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=1.[CH3:17][S:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>>[CH3:17][S:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[CH2:6][CH2:5][CH2:4][C:3]=2[C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)=[CH:21][CH:20]=1

참가 물질

3

반응물 2

HCID 27339594-(Methylthio)phenylboronic acidHCID 10470117Benzene, 1-(2-bromo-1-cyclopenten-1-yl)-4-(methylsulfonyl)-

생성물 1

HCID 99242511-Methylsulfanyl-4-[2-(4-methylsulfonylphenyl)-1-cyclopentenyl]benzene수율 86%

실험 절차

Following a synthetic procedure which was similar to the one outlined in Step 3 of Example 1, 270 mg (0.9 mmol) of 1-(2-bromocyclopenten-1-yl)-4-(methylsulfonyl)benzene (Step 1) was reached with 300 mg (1.8 mmol) of 4-methylthiophenylboronic acid (Example 1, Step 1). Purification by silica gel chromatography (MPLC) with hexane/ethyl acetate (4:1) gave 265 mg (86%) of 1-[2-(4-methylthiophenyl)cyclopenten-1-yl)-4-(methylsulfonyl)benzene as a colorless solid: mp 138°-139° C.; NMR (CDCl3) d 2.08 (m, J=7 Hz, 2H), 2.47 (s, 3H), 2.90 (t, J=7 Hz, 4H), 3.04 (s, 3H), 7.06 (d, J=8 Hz, 2H), 7.11 (d, J=8 Hz, 2H), 7.34 (d, J=8 Hz, 2H), 7.75 (d, J=8 Hz, 2H); ME (EI) m/e (rel intensity) 344 (100), 297 (4), 218 (33); HRMS. Calc'd for C19H20O2S2 : 344.0905. Found: 344.0907. Anal, Calc'd for C19H20O2S2 : C, 66.24; H, 5.85; S, 18.16. Found: C, 66.28; H, 5.81; S, 18.95.

후처리

  1. customPurification by silica gel chromatography (MPLC) with hexane/ethyl acetate (4:1)

출처 및 근거

ORD 기록
ord-3c2a90af584346cdba54ac284e53ddea
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420287

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